Is Chicago a worthwhile quick weekend trip or is it a similar experience to a major US big city (Nyc, sf, dc)?

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It’s an excellent weekend trip. The buildings are not “mostly squares”, there is a very interesting variation in architecture and I highly recommend taking one of the popular architectural tour boat rides down the river through downtown. Rooftops and patios along the water this time of year are a blast. Cold cities seem to know how to do summer right. You can rent a boat to take on gorgeous Lake Michigan as well. I’d say it actually has a surprising amount to offer and a unique character worth experiencing. It’s like if NYC were a bit smaller/more accessible, pleasant, a little more blue collar. I might be partial because I live in NYC and grew up in the Great Lakes region, but I really think Chicago is special.

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That building is essentially a square. Otherwise I agree with all of this.

Not really following the question - the only thing the cities you listed have in common is that they are cities. Do you think SF is not worth visiting bc you’ve seen DC already? Or vice versa? All of these cities (and Chicago) are incredibly different, why do you think visiting one means you shouldn’t go anywhere else?

likesmart

Depends what time of year 🙃

April - November - it’s wonderful with its own vibe.
December - March - you aren’t going outside so it’s like any other city.

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Definitely worth a weekend trip and might inspire you to come back for a longer one. Architectural boat tour on the river is a must (there are longer versions that also take you out on the lake for a skyline view), check out millenium park, buckingham fountain, and the lakefront bike trail. Uber to west loop for dinner and drinks one night. Skip navy pier and Willis tower ledge. You probably won’t have time to leave downtown in a short weekend but that would be next.. Lincoln park zoo (free), etc.

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It has some great museums and great food, but the people speak English and the buildings are mostly squares.

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There's a very cool circle building in Rome. I think it was an arsenal or something like that. Colosseum is a really nice circle building. The Pantheon is good. Also the new Tesla restaurant is circly, but probably speaking English so can't recommend.

Just came back from Chi - Update:

It’s IMO a truly world class city. Just had the best time that could not be replicated. And will be going back again.

uplifting

Just got back from a weekend trip in Chicago and I LOVED it. I’m from Jersey so grew up going to NYC often. The weather was in the mid 70s and I had such a good time. Similar feel to NYC but smaller which is nice cause it made it easy to get around

Any recommendations (restaurant, activity, venue) for something you miss there and can’t get in nyc?

Ancient planetarium is a really cool stop if you're into that

I’m from CA and I love Chicago and NYC. I would visit both over and over again (never been to Chicago in winter…but late fall-November). There is much to experience in both. Never bored and never gets old!

Yep good weekend trip, just did it last weekend

Ironically just did a weekend in Chicago and I loved my time here. Big city like NY but cleaner and amazing food places

Go to Toronto or Montreal instead.

That may be your opinion but I would wager most people would disagree. Some of those factors only matter if you’re living there and I would still argue I would rather live in Chicago. Nonetheless, OP was asking about visiting and from that perspective, Toronto doesn’t hold a candle to Chicago

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